Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/43—Thickening agents
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
  • C08L75/04—Polyurethanes

Definitions

• the present invention relates to an aqueous concentrate of an associative thickening polymer, said concentrate containing a nonionic surfactant as viscosity-reducing agent.
• a nonionic surfactant as viscosity-reducing agent.
• associative thickening polymers contain hydrophobic groups, they have the capacity of forming intermolecular hydrophobic associations, and adsorbing on the surfaces of dispersed particles. As a result, the associative polymers have a much greater thickening effect than the corresponding polymer having the same molecular weight and no hydrophobic groups. It is known that associative polymers are difficult to prepare in the form of highly concentrated aqueous solutions with such a low viscosity as to allow easy pumping and dosing. A way of solving the problem is to add organic solvents, which, however, should be avoided since they are highly volatile and cause environmental problems.
• EP-A-618 243 states that a combination of a nonionic compound and an acetylene diol with triple bond results in improved viscosity. As appears from the examples, an approximate addition of 15-22% by weight of the nonionic compound and 1-5% by weight of the acetylene compound is necessary for a concentrate containing 18.5-25% by weight of an associative polymer and having a viscosity below 10,000 mPa's to be obtained.
• EP-A-682 094 also states that anionic surfactants can be used, but they often cause undesired frothing and undesired effects in certain applications. For example, when present in colour compositions, they result in a dried colour coat with reduced water resistance.
• EP-A-460 896 discloses the use of cyclodectrin to reduce the viscosity of an aqueous associative thickening agent.
• An object of the present invention is to be able to prepare an aqueous concentrate of associative thickening agents having low percentages of viscosity-regulating additives, which to a small degree affect subsequent applications. They should not cause turbidity in the coating compositions and their dried layers. A further desideratum is that the additives should not cause frothing and that they should be easily biologically degradable and nontoxic.
• nonionic surfactant having a hydrophilic group consisting of ethyleneoxy groups as well as propyleneoxy groups.
• the nonionic surfactants comprised by the invention have the general formula RO AO H (I) wherein R is an alkyl group having 6-12, preferably 7-10 carbon atoms and AO is an ethyleneoxy or propyleneoxy group, the ratio of the ethyleneoxy groups to the total number of ethyleneoxy and propyleneoxy groups being from 1:2 to 5:6, preferably from 8:13 to 4:5, and a is a number between 7 and 16, preferably between 8 and 14.
• nonionic surfactants have froth-preventing properties while at the same time they have a surprisingly good viscosity-reducing capacity. They are also readily soluble in water. This means that the surfactant, after migrating to the colour film surface, is more easily washed away in rain. As a result, the stickiness of the colour film surface and its tendency to bind carbon black and dirt are reduced.
• the alkyleneoxy groups of the nonionic adduct can be added at random or in blocks, or as a combination of random adding and adding in blocks.
• first ethylene oxide is added to the alcohol, and then propylene oxide.
• These nonionic surfactants can be illustrated with the formula ROfEO)- ⁇ fPO)- p H wherein R has the above meaning, EO designates an ethyleneoxy group and PO a propyleneoxy group, e and p are numbers, of e and p being 7-16, preferably 8-14 and the ratio of e/e+p being from 1:2 to 5:6, preferably from 8:13 to 4:5.
• the aliphatic group R can thus be branched as well as straight although branched aliphatic groups are preferred since they have surprisingly been found to give an essential contribution to the viscosity reduction.
• branched groups are those comprised by the formula CpHap ⁇ CHCHa- (II) -oHanH-i wherein m and p are at least 2 and the sum of m+p+2 is 8-10, such as 2 ethyl hexyl or 2-propyl heptyl; or an alkyl group, the alkyl chain containing 2-4, preferably 2-3 groups having the formula -CH(CH 3 )- and 8-11 carbon atoms.
• the nonionic surfactants of formula I can be prepared in a conventional manner.
• an alcohol of the formula ROH can be alcoxylated in the presence of e.g. an alkali catalyst.
• an alkali catalyst In the alcoxylation, use of a so-called narrow range catalyst is preferred owing to the fact that the resulting alcoxylate contains lower percentages of unreacted alcohol. If desired, also unreacted alcohol can be removed, for instance, by distillation.
• the invention also concerns an aqueous concentrate of an associative polymer, the concentrate having a Brookfield viscosity, measured at 23 °C and 12 rpm, of 100-20,000 cP, preferably 200-10,000 cP.
• the concentration contains 10-50, preferably 15-45% by weight of an associative polymer and 1-25%, preferably 1-15% by weight of the nonionic surfactant according to formula I.
• the weight ratio of the associative polymer to the nonionic surfactant usually is 15:1 to 2:1 although a higher percentage of the nonionic surfactant, e.g. up to 3:2, can be used. This may be considered when the concentrate contains very high percentages of an associative polymer, for instance, above 35% by weight.
• associative polymers are ethyleneoxy-group-containing polyurethane, block polymers, alkali-soluble acrylates, copolymers and anionic or nonionic cellulose ethers, in which hydrophobic groups, such as hydrocarbon groups, have been incorporated.
• the hydrophobic groups are at least two and can be located in the ends of the polymer, in the polymer chain or as groups pendant from the polymer chain.
• the hydrophobic groups are usually hydrocarbon groups having 6-22 carbon atoms capable of forming micelle-like aggregates.
• Preferred associative thickening polymers are nonionic polymers.
• Examples of associative polymers which are comprised by the present invention are disclosed in EP-A-11 806, EP-A-57 875, EP-A- 248 612, EP-A-250 943, EP-A-310 345, EP-A-390 240, US 4,079,028, US 4,228,277, 093/24577 and O94/6840.
• the molecular weight of the associative polymers is suitably from 4,000 to 100,000 although polymers having a higher molecular weight can be used.
• the associative polymers are as a rule used as thickening agent in binder-containing coating compositions, such as water-based paper coating agents and water-based varnish and paint compositions.
• Suitable binders are emulsion binders, such as alkyd resins, and latex binders, such as polyvinyl acetate, polyacrylates, copolymers of vinyl acetate and aerylate, copolymers of vinyl acetate and ethylene, copolymers of vinyl acetate, ethylene and vinyl chloride, copolymers of styrene and acrylates, and copolymers of styrene and butadiene.
• the latex binders are usually stabilised with anionic surfactants.
• the associative polymers containing adducts of formula I have been found to be especially well suited for use in varnish and paint compositions containing latex binders.
• Example 1 The present invention is further illustrated by the following Examples.
• Example 1 The present invention is further illustrated by the following Examples.
• Example 1
• a varnish was prepared by mixing a varnish based on a polyurethane solution containing 9 parts of water and 1 dl of the polyurethane concentrate according to tests 1-8 with 1 mmole of a surfactant per g of polyurethane according to the Table below.
• the resulting varnish was applied with a thickness of 200 mm on glass plates and was allowed to dry.
• the gloss of the varnish layers was measured against a white background by measuring the reflectance at 85°C.
• the clearness of the varnish was assessed visually on a scale divided into two degrees. The following results were obtained.
• Example 2 20% concentrates of commercial associative polyurethane polymer (Rheolate 208 supplied by Reox Inc.) were prepared. The Brookfield viscosity of the concentrates was determined, and the following results were obtained.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Detergent Compositions (AREA)
• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

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• 1998
  • 1998-06-30 SE SE9802329A patent/SE512220C2/sv not_active IP Right Cessation
• 1999
  • 1999-01-07 US US09/226,531 patent/US6150445A/en not_active Expired - Fee Related
  • 1999-01-29 AU AU25544/99A patent/AU2554499A/en not_active Abandoned
  • 1999-01-29 JP JP2000557297A patent/JP2002519460A/ja active Pending
  • 1999-01-29 ES ES99905386T patent/ES2220044T3/es not_active Expired - Lifetime
  • 1999-01-29 EP EP99905386A patent/EP1093488B1/de not_active Expired - Lifetime
  • 1999-01-29 CA CA002333970A patent/CA2333970C/en not_active Expired - Fee Related
  • 1999-01-29 CN CN99807640A patent/CN1122682C/zh not_active Expired - Fee Related
  • 1999-01-29 WO PCT/SE1999/000010 patent/WO2000000539A1/en active IP Right Grant
  • 1999-01-29 DE DE69916451T patent/DE69916451T2/de not_active Expired - Lifetime

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